4-丁-1-烯基-吗啉 | 94608-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 中文名称: 4-丁-1-烯基-吗啉
• 英文名称: 4-but-1-enyl-morpholine
• 英文别名: 4-[(Z)-but-1-enyl]morpholine
• CAS: 94608-07-8
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: UTCCARLHJKAWIA-ARJAWSKDSA-N

物化性质

• 沸点：
  215.7±29.0 °C(predicted)
• 密度：
  1.001±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-丁-1-烯基-吗啉 、 N-甲基甲酰苯胺 在 ammonium hexafluorophosphate 、 三氯氧磷 作用下， 生成 hexafluoro-l6-phosphane, 3-ethyl-1-methylquinolin-1-ium salt
  参考文献：
  名称：

  The reverse vilsmeier approach to the synthesis of quinolines, quinolinium salts and quinolones

  摘要：

  N-Methylformanilide(MFA) reacts with various electron-rich alkenes in POCl3 solution to give N-methylquinolinium salts generally in good yield. The alkenes can be vinyl acetate, an aldehyde or ketone enamine (preferably the morpholine enamine), a methyl aryl ketone (reacting as its enol) or it may be generated from an alkanoamide bearing alpha-protons (which produces an alpha-chloroenamine in situ). The reaction is effective for a variety of other alkyl-, aryl- and benzyl- formanilides as well as ring substituted anilides though electron-withdrawing groups tend to inhibit cyclisation. The mechanism of the cyclisation has been elucidated and shown to involve an electrocyclic ak process. The reactions of MFA with amides in POCl3 gives 4-quinolones on alkaline workup.

  DOI：

  10.1016/0040-4020(95)00729-r
• 作为产物：
  描述：

  吗啉 、 正丁醛 以 甲苯 为溶剂， 反应 10.0h， 生成 4-丁-1-烯基-吗啉
  参考文献：
  名称：

  (±)-Vincamine 和 (±)-Eburnamonine 的全合成

  摘要：

  摘要 报道了长春胺 (1) 和乙萘胺 (2) 的合成，其中涉及到关键中间体 (8) 的新途径。

  DOI：

  10.1515/znb-1982-0624

文献信息

• 4-Dimethylamino-1-trifluoracetyl-pyridinium-trifluoracetat: Ein effizientes Reagens zur Synthese von Trifluormethyl-1,3-dicarbonyl-Verbindungen
  作者：Gerhard Simchen、Andreas Schmidt

  DOI：10.1055/s-1997-1501

  日期：1997.1

  4-Dimethylamino-1-trifluoroacetylpyridinium Trifluoroacetat: An Efficient Reagent for the Preparation of Trifluoromethyl-1,3-Dicarbonyl CompoundsEnamines 2 and O-trimethylsilyl ketene acetals 4 are trifluoroacetylated on reaction with the title reagent to yield trifluoroacetyl enamines 3 and trifluoromethylsilylenol ethers 5, respectively. Trifluoromethyl 1,3-diketones 6 and trifluoromethyl β-keto esters 7 are obtained by hydrolysis of compounds 3 and 5.

  4-Dimethylamino-1-trifluoroacetylpyridinium Trifluoroacetat：烯胺 2 和 O-三甲基硅酮乙醛 4 在与标题试剂反应时发生三氟乙酰化反应，分别生成三氟乙酰基烯胺 3 和三氟甲基硅醇醚 5。化合物 3 和 5 经水解可得到三氟甲基 1,3-二酮 6 和三氟甲基 δ-酮酯 7。
• Opitz,G.; Griesinger,A., Justus Liebigs Annalen der Chemie, 1963, vol. 665, p. 101 - 113
  作者：Opitz,G.、Griesinger,A.

  DOI：——

  日期：——
• Eicher,T.; Born,T., Justus Liebigs Annalen der Chemie, 1972, vol. 762, p. 127 - 153
  作者：Eicher,T.、Born,T.

  DOI：——

  日期：——
• VILSMAIER E.; TROEGER W., SYNTHESIS, 1980, NO 6, 466-469
  作者：VILSMAIER E.、 TROEGER W.

  DOI：——

  日期：——
• The reverse vilsmeier approach to the synthesis of quinolines, quinolinium salts and quinolones
  作者：Otto Meth-Cohn、David L Taylor

  DOI：10.1016/0040-4020(95)00729-r

  日期：1995.11

  N-Methylformanilide(MFA) reacts with various electron-rich alkenes in POCl3 solution to give N-methylquinolinium salts generally in good yield. The alkenes can be vinyl acetate, an aldehyde or ketone enamine (preferably the morpholine enamine), a methyl aryl ketone (reacting as its enol) or it may be generated from an alkanoamide bearing alpha-protons (which produces an alpha-chloroenamine in situ). The reaction is effective for a variety of other alkyl-, aryl- and benzyl- formanilides as well as ring substituted anilides though electron-withdrawing groups tend to inhibit cyclisation. The mechanism of the cyclisation has been elucidated and shown to involve an electrocyclic ak process. The reactions of MFA with amides in POCl3 gives 4-quinolones on alkaline workup.